Question 1

What is WaypointCareer?

Accepted Answer

WaypointCareer is a Career Intelligence platform — not a job board. It runs four loops in one place so your career growth is a continuous practice, not a panic when you suddenly need to move: Career growth — set goals across Daily / Weekly / Bi-Weekly / Monthly / Quarterly / Semi-Annual / Annual cadences, run periodic self-evaluations across six leadership domains, and keep a reading + reflection log of books, articles, and videos. Most metrics auto-track from your existing activity so you don’t double-log. Market awareness — see what your target roles pay, what skills they ask for, where the trend is heading. Watchlists for the companies you care about even when you aren’t looking. Always interview-ready — AI prep, question banks, round tracking, post-round debrief, thank-you-note drafts. Job search (when the time is right) — a personalised radar pulling from 20+ sources, a 9-stage pipeline, deadline tracking, document management, and AI-assisted application Q&A. You don’t have to be actively looking. The platform is built for Manager → Director → VP → SVP → C-suite — and it’s just as useful for a VP sharpening their leadership narrative as for a Director running a focused search.

Question 2

Do I need to pay to use it?

Accepted Answer

No — a Free plan is available with no card on file. You get access to public job sources, a limited number of keywords and locations, 1 active goal, 30-day job retention, and a small monthly AI allowance. Upgrade to one of three career-level tiers (Managerial, Leadership, Executive) when you need higher caps and more capabilities — see /pricing .

Question 3

How do I sign up?

Accepted Answer

Go to Register , enter your name, email, and a password. Sign-up never asks for a credit card. If you forget your password later, use Forgot password — you will receive an emailed one-time link valid for 30 minutes.

Question 4

Is my data private?

Accepted Answer

Every job, note, activity entry, and AI transcript is scoped to your user account. The platform is explicitly per-user multi-tenant — there is no shared job pool between accounts. Administrators can see aggregate counts and manage catalog content (ATS companies, pricing, title aliases, question bank) but they do not see your jobs, notes, or AI conversations. For AI specifically, prompts run on WaypointCareer's platform provider keys by default; if your admin enables a self-hosted Local (private) endpoint, you can choose it to keep every prompt on our own infrastructure with no third-party egress.

Question 5

What plans do you offer?

Accepted Answer

Four plans — Free plus three career-level tiers tuned for different audiences: Free — try the platform with 3 keywords, 1 location, 1 active goal, 30-day job retention, and a small monthly AI allowance (3 tips · 1 prep · 10 actions). Managerial — for Managers and Directors. 10 keywords, 5 locations, 5 active goals, 90-day retention, 25 AI tips + 10 prep + 100 AI actions per month. $19/mo or $190/yr. Leadership — for VP / SVP / GM. 25 keywords, 10 locations, 15 active goals, 1-year retention, 100 AI tips + 50 prep + 400 AI actions per month, Apify catalog, thought-leadership goal templates. $39/mo or $390/yr. Executive — for C-suite and Board. Unlimited everything (AI on a large fair-use allowance — 1,000 tips · 500 prep · 2,000 actions), executive-only goal templates, priority support. $69/mo or $690/yr. AI coaching is included in every plan — your tier gives a monthly allowance, and you can buy more usage anytime without changing plans (see the AI-usage FAQ below). Annual saves you roughly two months. See Pricing for the full feature comparison.

Question 6

Can I buy more AI usage if I run out?

Accepted Answer

Yes. Every plan — including Free — includes a monthly AI allowance that resets at the start of each calendar month. If you exhaust it before the reset, you can buy a one-time credit pack from Settings → Subscription without changing tiers. Credits never expire — they roll over month to month. Your monthly tier allowance is always used first, and credits only draw down once that allowance is spent. Heavier actions cost proportionally more (an interview-prep session draws more than a single tip), so a pack stretches across whatever mix of AI tools you use.

Question 7

Which tier should I pick?

Accepted Answer

The simplest rule: buy the tier that matches the role you’re aiming for. A VP role hunt isn’t really helped by Managerial-tier caps; a Manager role hunt doesn’t need Executive-tier templates. If you’re between tiers, default to Leadership — it’s the middle option and fits the most use cases. You can always upgrade or downgrade later from Settings → Subscription.

Question 8

I had a PRO subscription — what happened?

Accepted Answer

Before April 2026 the platform shipped with a single paid tier called PRO. When the three-tier model launched, every PRO subscriber was migrated to Leadership (the middle tier — fairest default; nobody lost access). If you were on PRO and want a different tier, switch any time from Settings → Subscription.

Question 9

How do I subscribe or change tier?

Accepted Answer

From Settings → Subscription , click Compare tiers to land on the pricing page. Pick your tier and Monthly / Annual cycle. Checkout is handled by Stripe on their hosted page — WaypointCareer never sees your card details. Your plan flips to the new tier as soon as Stripe confirms payment.

Question 10

Can I cancel anytime?

Accepted Answer

Yes. Cancel from Settings → Subscription → Manage billing which opens the Stripe Customer Portal. Your plan stays at the current tier until the end of the paid period, then drops back to Free automatically.

Question 11

What billing periods are available?

Accepted Answer

Monthly, quarterly, semi-annual, and annual — the longer terms carry progressively larger discounts. Live pricing lives at Pricing ; admins can adjust it without a code deploy.

Question 12

Can I delete my account?

Accepted Answer

Yes — from Settings → Account → Delete account . All your jobs, activity, documents, AI sessions, and API keys are removed. A soft-delete flag immediately locks the account out; the hard purge runs on a short schedule.

Question 13

What are Goals?

Accepted Answer

Goals are measurable career-growth targets you commit to across seven cadences — daily, weekly, bi-weekly, monthly, quarterly, semi-annual, and annual. The platform tracks progress automatically wherever it can — applications submitted, books finished, contacts touched, self-evaluations completed — so you don’t end up logging the same activity twice. Manage them at /goals .

Question 14

What are templates and why use them?

Accepted Answer

Pre-built starting points organised by category — Search, Networking, Brand, Learning. Click From template on the Goals page to browse the 22-template library; the “Suggested” tab is keyed off your career status (3 picks tuned to where you are). Each template populates the editor — you can adjust target, cadence, and title before saving.

Question 15

How do period boundaries work?

Accepted Answer

Periods are calendar-aligned, not rolling: Daily — midnight to midnight (your local time) Weekly — Sunday → Saturday Bi-Weekly — 14-day windows anchored to the first Sunday of the year Monthly — 1st of the month → end of the month Quarterly — Q1 (Jan–Mar), Q2 (Apr–Jun), Q3 (Jul–Sep), Q4 (Oct–Dec) Semi-Annual — H1 (Jan–Jun), H2 (Jul–Dec) Annual — Jan 1 → Dec 31 A goal you create mid-period is credited for everything already done in the current period — so adding a “1 self-eval per quarter” goal right after completing one reads 1 / 1, not 0 / 1. From the next period on, progress counts from the period’s own start.

Question 16

What's a manual goal vs an auto-tracked one?

Accepted Answer

Most metrics auto-derive from activity the platform already sees (applications submitted, books finished, contacts added, self-evaluations completed). A handful are manual — board meetings, public speaking, mentorship sessions, executive coaching, custom — because there’s no upstream signal to derive them from. Manual goal cards show a + button to log entries; you can backdate and add a note.

Question 17

How many goals can I have?

Accepted Answer

Active-goal caps scale by tier: Free = 1, Managerial = 5, Leadership = 15, Executive = unlimited. Paused and archived goals don’t count — if you’re at the cap and want to try a new goal, pause one of your existing ones to preserve its history.

Question 18

What is Self Evaluation in WaypointCareer?

Accepted Answer

A structured 150-question rubric you work through one question at a time. Questions span six leadership domains — Technical , AI / ML , Operational , Organizational , Executive , and Strategic — calibrated against five career levels (Manager, Director / Head, VP, SVP, C-Level). Each prompt carries behavioural anchors describing what a 5/5 actually looks like at your target level, so you’re not guessing what “strong” means. The catalog is admin-curated — see Admin → Evaluation Questions .

Question 19

How are evaluations scored?

Accepted Answer

Each answer is a 1–5 rating against the anchor. Scores aggregate per domain and render as a bar chart so you can see, at a glance, which of the six domains is your floor and which is your ceiling. Re-runs sit alongside prior attempts so you can track movement over time rather than just a single snapshot.

Question 20

How often can I run a new evaluation?

Accepted Answer

Cadence scales by tier — the more senior the seat, the faster you’re expected to recalibrate: Free — yearly Managerial — every 60 days Leadership — every 30 days Executive — every 14 days The cooldown counts from when you complete an evaluation, not when you start it — so a draft you take weeks to finish doesn’t burn the window. If you’re inside the cooldown, the disabled Start button shows the next eligible date on hover.

Question 21

Why does the question set change based on my target level?

Accepted Answer

A 5/5 looks different at every level. “Owns the roadmap” means something concrete for a Manager and something completely different for a C-Level. The anchors and the subset of the 150 questions you see are tuned to the level you’re evaluating against — so the rating is honest rather than flattering.

Question 22

Can I skip a question and come back?

Accepted Answer

Yes. The stepper has Skip , Previous , and Next . Per-domain progress chips along the top show how much of each domain you’ve covered so it’s easy to circle back to a skipped one before finalising the run.

Question 23

What is "Build Your Brand"?

Accepted Answer

The set of surfaces that turn you from a candidate into a known person in your field — before any board, recruiter, or search committee starts looking. It bundles: A 4-question Brand Voice assessment — AI summarises the topic, stance, and tone you write from. A public, Googleable profile at /profile/<slug> . Pipelines for Pitches , Media Mentions , a Reading List , Networking Contacts , and Search Firms . The whole suite is gated to Leadership and Executive tiers — it maps to the work senior operators do every week whether or not they’re hunting.

Question 24

What is the Brand voice assessment?

Accepted Answer

A short, 4-question survey that captures the topic you write about, the stance you take on it, and the tone you use. The AI then produces a one-paragraph summary (“your voice in one breath”) that becomes context for downstream drafting — pitches, profile copy, posts. Completion is tracked on BrandProfile.voiceCompletedAt so the rest of the brand surfaces unlock once it’s done.

Question 25

What's on my public profile page?

Accepted Answer

A subscriber-controlled landing page at /profile/<slug> : slug, photo, headline, bio, social links, plus published Pitches, Mentions, and a curated slice of your Reading List. Visible to anonymous visitors — board search committees, journalists, recruiters — without them needing an account. Pages are served with ISR ( revalidate=300 ) so edits propagate within five minutes. A noIndex flag opts the page out of search engines if you’d rather it stay shareable but un-Googleable.

Question 26

How are Pitches different from job applications?

Accepted Answer

A Thought Leadership Pitch is something you initiate — an article pitched to an outlet, a conference talk proposal, a podcast appearance request. The statuses mirror the job pipeline (Pending → Submitted → In Review → Accepted / Declined) so the muscle memory is the same, but the upstream actor is you, not a recruiter. Pitches live in their own table ( ThoughtLeadershipPitch ) and don’t pollute your job pipeline.

Question 27

What's the difference between a Pitch and a Media Mention?

Accepted Answer

A Pitch is outbound — you proposed something. A Media Mention is inbound — a press citation, a speaking invite, an award, a quote in someone else’s article. Mentions can also record downstream outcomes (e.g. “led to a board interview”) so a single citation isn’t just a trophy — it’s a tracked source of pipeline.

Question 28

How does the Reading list build my brand?

Accepted Answer

ReadingItem is your book + article library; each item carries timestamped ReadingNote entries so you can write as you read instead of trying to remember a quarter later. Cross-item view surfaces patterns across what you’ve consumed; AI summaries are available on demand. The published slice on your public profile signals taste — and a body of notes you can quote from is the cheapest pitch fuel there is.

Question 29

What are Memorable Experiences for?

Accepted Answer

A library of professional stories you can reach for in scenario-based interviews and presentations. Write each one free-form in your own voice; tag it by skill domain (the same six the Self-Evaluation uses) and target career level. When you need a structured version, click Format with AI and the system converts the body into STAR (Situation / Task / Action / Result + Lessons). The AI won’t invent facts not in your text. Before a behavioral interview round, filter to your EXECUTIVE -level OPERATIONAL stories and you have a deck ready.

Question 30

Where do I capture standalone notes and quotes?

Accepted Answer

LibraryNote is the standalone-capture surface for anything that isn’t a book / article / video in your reading list. One model, two kinds — NOTE for free-form observations, QUOTE for memorable lines with attribution. Search across title / content / attribution; filter by tag. If the note belongs to a reading-list item, keep it scoped to that item via the existing ReadingNote drawer instead.

Question 31

Can I dictate instead of typing? Where does the audio go?

Accepted Answer

Yes — long-form fields (experience body, note content, interview answers, self-eval reflections, pitch bodies, goal descriptions, and more) all have a Dictate button. Transcription happens entirely in your browser via the Web Speech API. No audio is ever sent to or stored by WaypointCareer. The privacy promise is structural — there’s no server-side audio path. Works in Chrome, Edge, and Safari; on Firefox the button is hidden because the API isn’t available.

Question 32

How does the weekly / monthly digest work?

Accepted Answer

New accounts default to Weekly . Each digest summarises your progress (goal hit-rate over the window), active goals, top two pending articles and top two pending videos in your reading list, a nudge if you haven’t self-evaluated in 90 days, and any platform announcements. Switch to Monthly or Off at any time from Settings → Notifications, or one-click unsubscribe from the footer of any digest. If the assembled digest has nothing meaningful to report, it’s skipped — you won’t train yourself to ignore empty mail.

Question 33

What's the difference between a Networking Contact and an Amplifier?

Accepted Answer

Both live in NetworkingContact , but the type tells you why you’re talking to them. A Contact is a senior peer — a potential hiring manager, a board member, an executive in your target market. An Amplifier is someone who multiplies reach — a journalist, a conference organiser, a newsletter author. Both surface in touched-this-period metrics for the goals system, and logging a coffee against either auto-refreshes their last-touched date.

Question 34

How are Search Firms different from regular contacts?

Accepted Answer

SearchFirm tracks executive recruiters as firms, not individuals — a firm has a region, an industry, and a list of partners you’ve touched. The platform also suggests firms by industry / region using AI so you’re not starting from a blank sheet. Touchpoint tracking is dated so you can see which firms have gone cold.

Question 35

How is my brand data kept private?

Accepted Answer

Pitches, Mentions, Reading notes, Contacts, and Search Firm touchpoints are private by default — only the published-on-profile flag exposes any record publicly. The brand-reports feature on each public profile lets anonymous visitors flag a profile (impersonation, policy issue, stale info); admins triage at /admin/brand-reports . The same per-user multi-tenant rules that protect your job data apply to every brand surface.

Question 36

Can I take my profile offline temporarily?

Accepted Answer

Yes. Flip the profile to inactive and the public URL renders a “temporarily inactive” state instead of your content. Useful when you’re between roles and don’t want a stale headline indexed, or when you’re in a quiet window before a public move.

Question 37

What tiers can use Build Your Brand?

Accepted Answer

Leadership and Executive only. Free and Managerial subscribers see the surface locked with an upgrade hint — the brand work is the leverage that justifies the higher tiers, so it’s priced accordingly.

Question 38

What is on the Dashboard?

Accepted Answer

Today and weekly plan progress, pipeline counts (Pending Review, Interested, Applied, Interviewing, Offers), upcoming deadlines, and recent activity. It is the fastest way to see what's worth touching today.

Question 39

What is "Retrieved" vs "Matched"?

Accepted Answer

Retrieved is the raw total of job postings pulled from every provider in a fetch window. Matched is the subset that passed your filters (keywords, locations, salary floor, title exclusions). Retrieved is the funnel's top; Matched is what you actually see in your pipeline.

Question 40

How do I export my data?

Accepted Answer

From Job Search , click Export CSV . The export respects your current status-tab filter. CSV export is available on every paid plan (Managerial, Leadership, Executive); Free users see the button disabled with an upgrade prompt.

Question 41

How do I upload a resume?

Accepted Answer

Resume in the sidebar. Upload a PDF or DOCX; we extract the plain text and store it. The parsed text feeds AI prep, tips, and the application-Q&A / interview-prep draft features so answers are grounded in your actual experience.

Question 42

What's the difference between Resume and Job Documents?

Accepted Answer

Resume is your default, current resume — its parsed text becomes AI context. One active resume at a time. Job Documents are per-job attachments (the resume variant you sent with that application, a cover letter, a portfolio). They are stored as files, not just parsed text, so you can download the exact bytes you submitted.

Question 43

What is Baseline Listing?

Accepted Answer

The original WaypointCareer surface — job board aggregation, pipeline tracking, interview prep, and document storage. This is the engine that runs in the background once your Brand and Self Evaluation practice is set up; most subscribers spend less time here as the Brand surfaces become daily habit.

Question 44

How do I set up my job search?

Accepted Answer

Search & Discovery Settings → Search Keywords and Settings → Locations . Keywords are role-style phrases (e.g. VP of Engineering ); locations are regions to consider (e.g. Remote , Seattle ). The matcher canonicalises titles before comparing — VP , V.P. , and Vice President all collapse to the same token via the admin-editable alias table.

Question 45

What are exclude words?

Accepted Answer

Phrases that, when found inside a job title that otherwise matched a keyword, cause the posting to be auto-hidden. Excluding Mechanical Engineering removes VP of Mechanical Engineering while still surfacing VP of Engineering . Manage at Settings → Job Preferences → Title exclusions .

Question 46

What does "Filtered" mean, and "Pending Review"?

Accepted Answer

Pending Review is the landing status for any new job — waiting for you to triage. Filtered postings failed a rule (title exclusion, minimum salary, location mismatch) and are suppressed from the pipeline tabs. To re-apply current rules to recent postings after tweaking filters, use Settings → Job Preferences → Re-filter last 30 days .

Question 47

I saw a job on LinkedIn — can I import it?

Accepted Answer

Yes, via Job Search → Add Job : URL — paste a job URL; works for Greenhouse, Lever, Ashby, Workable, most company career pages. Paste HTML — for sites that block server fetching (LinkedIn, Indeed, Glassdoor). Use the bookmarklet to grab the rendered HTML in one click. Add Manually — for referrals and sites with no structured metadata. If LinkedIn paste returns no job data found , try the URL in an incognito window — the logged-out variant ships richer metadata.

Question 48

Add Job says "Already in your pipeline (filtered: location)" — how do I fix it?

Accepted Answer

The posting is already on file but was filtered by LOCATION_MISMATCH — usually because the upstream listing didn't advertise itself as remote. Click Mark as Remote and restore on the duplicate banner. The existing row flips to remoteType=REMOTE , clears its filter reason, and returns to Pending Review. No second entry is created.

Question 49

What are the job statuses?

Accepted Answer

Pipeline & Tracking Pending Review → Interested → Applied → Interviewing → Offer . Terminals: Rejected , Closed , Not Relevant , Out of Region . The Kanban view at Job Pipeline is drag-and-drop; history is preserved on each job's Details tab.

Question 50

How do application deadlines work?

Accepted Answer

Set an Application Deadline on the Details tab. Jobs with deadlines render a colour-coded urgency tag (green > 7 days, amber 4–7, red ≤ 3 and overdue) in lists and on the Dashboard Upcoming deadlines card.

Question 51

How do I fix an inaccurate auto-fetched field?

Accepted Answer

Open the job, click Edit on the Company card. Location, salary range, currency, and description are all overridable. Corrections persist — the next fetch will not overwrite them.

Question 52

How does Interview Prep work?

Accepted Answer

Interview Prep + Documents Each job's Interview Prep tab has one sub-tab per scheduled round. Pull questions from your bank, write per-round answers, export to PDF. The bank at /interview-prep (My Question Bank) holds ~40 admin-seeded questions plus your private additions, with role tags so only the relevant subset surfaces on a given job. Answers reuse across jobs by default; Company-specific questions save per-job. AI Draft writes a 150–250 word first pass grounded in your resume; AI Tweak polishes existing text without inventing facts.

Question 53

How do document attachments work?

Accepted Answer

The Documents tab appears once a job is Interested , Applied , or Interviewing . Allowed types: PDF, DOC, DOCX, TXT, MD, PNG, JPG. Caps: Free = 2 docs / 2 MB each; paid tiers = 5 docs / 5 MB. PDF and DOCX uploads are text-extracted for future AI features. Files live in per-user directories outside the public web root — downloads go through an authenticated API.

Question 54

Where is cadence tracking?

Accepted Answer

Cadence tracking (Insights) Cadence tracking is part of the Insights page — no minute tracking. The This week tab shows the recommended rhythms for your career status (e.g. “ 5+ outreach per day”, “2 search firms per week”), each tagged Touched this week or Not yet . The Log activity tab records what you did — type ( Job Search , Skills , Interview Prep , Networking , Search Firms , Other ), optional subtype, linked contact / firm, source URL, title, and notes — and feeds the weekly cadence read-out plus an active-day streak. The question is whether you did it, not how long it took.

Question 55

How are passwords stored?

Accepted Answer

Hashed with bcrypt (10 rounds), with account lockout after 5 failed attempts in a rolling window. Plaintext passwords are never stored and never logged.

Question 56

I forgot my password. How do I reset it?

Accepted Answer

Go to Forgot password , enter your email, and we send a one-time link. The link is valid for 30 minutes, hashed server-side (the raw token never lands in our database), and invalidates on first use.

Question 57

What is the session timeout?

Accepted Answer

Sessions expire after 2 hours of inactivity. Two minutes before the expiry the app shows a warning modal with a live countdown. Click Stay signed in (or any key / mouse movement) to extend; do nothing and you are signed out automatically. The cookie itself is a 30-day JWT but the idle clock runs independently.

Question 58

Why did I get bounced to /login when I clicked a button?

Accepted Answer

Your session had already expired when the click fired. The app detects the 401 response, signs you out cleanly, and preserves the page you were on in the redirect URL — so logging back in lands you exactly where you left off.

Question 59

How are my AI provider keys stored?

Accepted Answer

AI is funded by the platform now — your plan's monthly allowance runs on WaypointCareer's own provider keys, which live in admin-controlled SystemParameter rows, not on your account. Adding your own provider key is optional (for unmetered use): if you do, it's encrypted at rest, decrypted only at call-time, never logged, and redacted from error messages. Job-source API keys are likewise platform-owned and under admin control.

Question 60

What is the Local (private) AI option?

Accepted Answer

Local is a self-hosted AI endpoint your administrator can run on WaypointCareer's own infrastructure (an OpenAI-compatible server such as Ollama, LM Studio, or vLLM). When it's enabled, a “Local (private)” choice appears in Settings → Profile → AI provider . Its advantage is privacy: every prompt is processed only on our own infrastructure with no third-party provider egress. Local usage still counts against your monthly AI allowance like the platform path, but carries no per-token cost. If your admin hasn't configured a Local endpoint, the option simply doesn't appear.

Question 61

No jobs are appearing after a fetch — what do I do?

Accepted Answer

Three common causes: No keywords yet. The matcher refuses to run against an empty keyword list. Add at least one at Settings → Search Keywords . Filters too tight. Postings can be auto-suppressed for reasons like TITLE_EXCLUDED , SALARY_BELOW_MIN , or LOCATION_MISMATCH . Loosen the relevant rule under Settings , then use Re-filter last 30 days to re-classify recent postings. Catalog is still filling. The platform ingest runs each source on its own cadence; rate-limited providers refresh only twice daily. New postings show up after the next matcher wave at 13:00 or 22:00 UTC (5 AM / 2 PM PST). Aggregate counts and source-level performance are visible on the Reports page (every paid tier unlocks Source Performance + Keyword Heatmap). Admins can see platform ingest health at Admin → Job Catalog .

Question 62

AI features keep failing — what now?

Accepted Answer

The error banner includes the reason (quota exceeded, rate-limited, service unavailable, model not available) and, when relevant, a link to the provider's console. On your plan's included AI: you may have used your monthly allowance — buy more usage from Settings → Subscription , switch your default AI provider in Settings → Profile , or wait out a transient rate-limit. A persistent platform-key outage is ours to fix — contact support. If you've added your own key: regenerate it, top up your provider account balance, or remove it to fall back to the included platform AI.

Question 63

The "View full posting" modal is blank.

Accepted Answer

The source site refuses to be framed (X-Frame-Options DENY or a frame-ancestors CSP). LinkedIn, Indeed, Glassdoor, and ZipRecruiter all do this. Click the Apply button on the header to open the posting in a new tab instead.

Question 64

The bookmarklet pops the dreaded 'React has blocked a javascript: URL'.

Accepted Answer

We fixed the install path in a recent release — reinstall from /bookmarklet . The button there sets the href post-mount to bypass React's security substitution.

Frequently Asked Questions

Getting started

Plans & billing

Goals

Self Evaluation

Build Your Brand

Dashboard & reports

Resume

Baseline Listing

Privacy, security, and sessions

Troubleshooting

Still have questions?